KR20240004735A - 3개 이상의 히드록시 기 및 5개 이상의 총 탄소 원자 수를 갖는 지방족 폴리올을 제조하는 방법 - Google Patents
3개 이상의 히드록시 기 및 5개 이상의 총 탄소 원자 수를 갖는 지방족 폴리올을 제조하는 방법 Download PDFInfo
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- KR20240004735A KR20240004735A KR1020237041156A KR20237041156A KR20240004735A KR 20240004735 A KR20240004735 A KR 20240004735A KR 1020237041156 A KR1020237041156 A KR 1020237041156A KR 20237041156 A KR20237041156 A KR 20237041156A KR 20240004735 A KR20240004735 A KR 20240004735A
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- South Korea
- Prior art keywords
- group
- product
- carbon atoms
- total number
- hydroxy groups
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- -1 aliphatic polyols Chemical class 0.000 title claims abstract description 258
- 125000004432 carbon atom Chemical group C* 0.000 title claims abstract description 158
- 229920005862 polyol Polymers 0.000 title claims abstract description 156
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title claims abstract description 135
- 238000000034 method Methods 0.000 title claims abstract description 63
- 239000007858 starting material Substances 0.000 claims abstract description 178
- 150000001875 compounds Chemical class 0.000 claims abstract description 115
- 150000002148 esters Chemical class 0.000 claims abstract description 85
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 68
- 150000003839 salts Chemical class 0.000 claims abstract description 68
- 239000003054 catalyst Substances 0.000 claims abstract description 67
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 claims abstract description 44
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 227
- 239000000047 product Substances 0.000 claims description 187
- 239000002904 solvent Substances 0.000 claims description 40
- 239000011541 reaction mixture Substances 0.000 claims description 33
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 claims description 30
- 229940091181 aconitic acid Drugs 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 30
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 27
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 25
- 239000000463 material Substances 0.000 claims description 23
- ODBLHEXUDAPZAU-UHFFFAOYSA-N threo-D-isocitric acid Natural products OC(=O)C(O)C(C(O)=O)CC(O)=O ODBLHEXUDAPZAU-UHFFFAOYSA-N 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- ODBLHEXUDAPZAU-FONMRSAGSA-N Isocitric acid Natural products OC(=O)[C@@H](O)[C@H](C(O)=O)CC(O)=O ODBLHEXUDAPZAU-FONMRSAGSA-N 0.000 claims description 22
- ODBLHEXUDAPZAU-ZAFYKAAXSA-N D-threo-isocitric acid Chemical compound OC(=O)[C@H](O)[C@@H](C(O)=O)CC(O)=O ODBLHEXUDAPZAU-ZAFYKAAXSA-N 0.000 claims description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 21
- 229910052707 ruthenium Inorganic materials 0.000 claims description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 18
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 18
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- 239000002184 metal Substances 0.000 claims description 18
- 229910052702 rhenium Inorganic materials 0.000 claims description 17
- OPWXOSDGXNFVNM-UHFFFAOYSA-N 3-(hydroxymethyl)pent-2-ene-1,5-diol Chemical compound OCCC(CO)=CCO OPWXOSDGXNFVNM-UHFFFAOYSA-N 0.000 claims description 16
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
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- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- LMMTVYUCEFJZLC-UHFFFAOYSA-N 1,3,5-pentanetriol Chemical compound OCCC(O)CCO LMMTVYUCEFJZLC-UHFFFAOYSA-N 0.000 claims description 13
- JLQQVSKMDDAFPK-UHFFFAOYSA-N 3-(hydroxymethyl)pentane-1,3,5-triol Chemical compound OCCC(O)(CO)CCO JLQQVSKMDDAFPK-UHFFFAOYSA-N 0.000 claims description 13
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 229910052763 palladium Inorganic materials 0.000 claims description 9
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- 150000007942 carboxylates Chemical group 0.000 claims description 8
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 7
- 229910052709 silver Inorganic materials 0.000 claims description 7
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- 235000013769 triethyl citrate Nutrition 0.000 claims description 5
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims description 3
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- 239000003575 carbonaceous material Substances 0.000 claims description 2
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- 229910044991 metal oxide Inorganic materials 0.000 claims description 2
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- 229910003465 moissanite Inorganic materials 0.000 claims description 2
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- 239000010457 zeolite Substances 0.000 claims description 2
- OGXRXFRHDCIXDS-UHFFFAOYSA-N methanol;propane-1,2,3-triol Chemical compound OC.OCC(O)CO OGXRXFRHDCIXDS-UHFFFAOYSA-N 0.000 claims 3
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 229960004106 citric acid Drugs 0.000 description 72
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 46
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 36
- 238000007086 side reaction Methods 0.000 description 16
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- 238000005984 hydrogenation reaction Methods 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
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- 238000006114 decarboxylation reaction Methods 0.000 description 10
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- 239000012467 final product Substances 0.000 description 5
- 239000013067 intermediate product Substances 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
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- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
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- KQTIIICEAUMSDG-UHFFFAOYSA-N tricarballylic acid Chemical compound OC(=O)CC(C(O)=O)CC(O)=O KQTIIICEAUMSDG-UHFFFAOYSA-N 0.000 description 2
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- SVNHEBUGYPWWOF-UHFFFAOYSA-N 2-(oxolan-3-yl)ethanol Chemical compound OCCC1CCOC1 SVNHEBUGYPWWOF-UHFFFAOYSA-N 0.000 description 1
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 1
- LJPCNSSTRWGCMZ-UHFFFAOYSA-N 3-methyloxolane Chemical compound CC1CCOC1 LJPCNSSTRWGCMZ-UHFFFAOYSA-N 0.000 description 1
- YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
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- QGLBZNZGBLRJGS-UHFFFAOYSA-N Dihydro-3-methyl-2(3H)-furanone Chemical compound CC1CCOC1=O QGLBZNZGBLRJGS-UHFFFAOYSA-N 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
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- 235000020971 citrus fruits Nutrition 0.000 description 1
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- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- YSNVSVCWTBLLRW-UHFFFAOYSA-N oxan-4-ylmethanol Chemical compound OCC1CCOCC1 YSNVSVCWTBLLRW-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
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- 239000002243 precursor Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/22—Trihydroxylic alcohols, e.g. glycerol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/24—Tetrahydroxylic alcohols, e.g. pentaerythritol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
- C07C33/025—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond
- C07C33/03—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond in beta-position, e.g. allyl alcohol, methallyl alcohol
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP21172092.5 | 2021-05-04 | ||
EP21172092 | 2021-05-04 | ||
PCT/EP2022/061908 WO2022233904A1 (en) | 2021-05-04 | 2022-05-04 | Method of preparing aliphatic polyols having three or more hydroxy groups and a total number of carbon atoms of 5 or more |
Publications (1)
Publication Number | Publication Date |
---|---|
KR20240004735A true KR20240004735A (ko) | 2024-01-11 |
Family
ID=75801513
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020237041156A KR20240004735A (ko) | 2021-05-04 | 2022-05-04 | 3개 이상의 히드록시 기 및 5개 이상의 총 탄소 원자 수를 갖는 지방족 폴리올을 제조하는 방법 |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP4334273A1 (zh) |
JP (1) | JP2024520194A (zh) |
KR (1) | KR20240004735A (zh) |
CN (1) | CN117255778A (zh) |
BR (1) | BR112023022950A2 (zh) |
WO (1) | WO2022233904A1 (zh) |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4233431A1 (de) | 1992-10-05 | 1994-04-07 | Basf Ag | Verfahren zur Hydrierung von Zitronensäure |
DE4444109A1 (de) * | 1994-12-12 | 1996-06-13 | Bayer Ag | Verfahren zur Herstellung von optisch aktiven Alkoholen |
US10301406B2 (en) | 2017-06-01 | 2019-05-28 | International Business Machines Corporation | Flame-retardant aconitic acid-derived monomers |
US10280287B2 (en) * | 2017-06-01 | 2019-05-07 | International Business Machines Corporation | Flame-retardant aconitic acid-derived small molecules |
-
2022
- 2022-05-04 BR BR112023022950A patent/BR112023022950A2/pt unknown
- 2022-05-04 WO PCT/EP2022/061908 patent/WO2022233904A1/en active Application Filing
- 2022-05-04 EP EP22727131.9A patent/EP4334273A1/en active Pending
- 2022-05-04 JP JP2023568168A patent/JP2024520194A/ja active Pending
- 2022-05-04 CN CN202280033126.1A patent/CN117255778A/zh active Pending
- 2022-05-04 KR KR1020237041156A patent/KR20240004735A/ko unknown
Also Published As
Publication number | Publication date |
---|---|
WO2022233904A1 (en) | 2022-11-10 |
JP2024520194A (ja) | 2024-05-22 |
BR112023022950A2 (pt) | 2024-01-16 |
EP4334273A1 (en) | 2024-03-13 |
CN117255778A (zh) | 2023-12-19 |
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